Dragon’s Den to the Snake Pit

Kevin O’Leary made front page news earlier this week with an offer to Alberta premier Rachel Notley. O’Leary would invest one million dollars in the oil and gas industry if the premier resigned. The offer was met with chuckles from the commentariat. O’Leary has made no secret of his displeasure with the governing NDP. Yesterday’s announcement of a CPC leadership bid came as a bit of a surprise, but the shock was quickly replaced with a curiosity about the feasibility of such an exercise. Michael Den Tandt offers a interesting take on his potential draw, and the role he could play in such a race.

I’ve worked a fair amount of campaigns. I’m more than convinced that the transition from business to politics can successfully be made. The goals may be loftier, the language softer, and the rules a bit more fuzzy, but the objective is the same. All it takes is a bit of time to ensure you know your new market. Den Tandt asks “Does O’Leary have a shot against party stalwarts such as…?”. To be frank, that is up to Kevin. Can he build the type of campaign that he will need to be successful? Is he destined to be Belinda Stronach or Brian Mulroney?

Somewhere, in some smoky back room in the Albany Club, there is not doubt a team of O’Leary insiders plotting his ascent to power. I’ve never been the smoky back room type, so figured I’d offer this online instead. Kevin, five free bits of advice. Take what you will, they’ve come a source that knows his stuff.

Take Risks, but Take Calculated Risks

There is far more to a leadership race than taking pot-shots at sitting premiers in the media. You’ll be taking a risk every time you open your mouth, and your opponents won’t cut you any slack. This is the type of race that is extraordinarily difficult to handicap. Difficult is not impossible. Know your key metrics before you begin. Don’t take stupid risks.

You will be building a brand that needs to resonate with the existing conservative membership, and can bring you the additional sales you need to win a plurality of votes in 338 ridings. You need 16,901 points. If a task, a team member, a trip, doesn’t get you closer to that goal, it may not be a risk worth taking.

Ask Howard Dean about the downside of poor communications strategy. Ask Ed Miliband what a single bad press conference visual can do to your vote. Ask Kim Campbell about the risks of a well funded advertising campaign. Ask Carly Fiorina about the risks of a playful tweet endorsing a college football team.

Assessing these risks requires different skillsets than chasing an investment return. Don’t assume you know these risks, and don’t assume the commentariat knows it either. How many times has Trump been written off for dead, and Hillary described as inevitable?

Assholes get elected because they aren’t afraid to ask for what they want

I’ve spent too much time in politics to put up with halfhearted candidates that aren’t sure if they want it. If this is something you want to do, do it. A political campaign is a grueling business. It takes thousands of hours from you, your staff & volunteers, and places considerable stress on you and your family. The running joke is that your IQ drops 30 points the moment your name goes on the ballot.

I’ve seen well-spoken, intelligent individuals crack under the stress, and others push through, immune to criticism and public scrutiny. Be damn sure you want this before you decide to put your name forward. That is the only thing that will keep you going when you hit the eventual challenges and pitfalls that bedevil any campaign.

You will be asking for money, and favours. You’ll be asking volunteers nation wide to give of their time and treasure. You need to be a confident ask. You are a value proposition that is incredibly hard to quantify. You need to know you are a worthwhile investment of their time and dollars, and you should be able to communicate that. A little bit of narcissism goes a long way.

Pair up with people whose strengths compensate for your weaknesses.

Your team will matter more than you know. You need people that can call you on your bullshit, establish connections for you across an extraordinarily large and diverse country, and provide advice on the ins and outs of internal party politics. You understand business, and the associated soft skills required for success. Most of those transfer nicely to politics, but your weaknesses will become readily apparent to the people around you. No politician is without them, but good staff can mitigate their damage.

A good campaign team is hard to find. In a business of bluster and bullshit, most campaign staff will drastically oversell themselves, their resume, and their skillset. It happens. Can you parse through a political resume to pick out what really matters? You’ve no doubt seen the star-studded campaign teams that flop horribly (See Belinda). They are as much a risk as the candidates that don’t listen to good advice and find themselves on the wrong side of the history books. Building your core team is just as important in politics as business. Choose wisely.

Know your numbers — 16,901

The late Senator Doug Finley used to say that you’ll never have enough of three things in politics. Time, Treasure, and Talent. You will need all three of these if you want a serious shot at the prize. Get an idea of how many staff you’ll need, how much you’ll need to fund raise, and how you’ll need to spend to have a credible shot. Ask any consultant working the GOP primary what they think about Ben Carson’s campaign direct mail program. The ROI is not what was desired (expect maybe for the firm).

Keep your eye on the prize, know what you need to do to win, and don’t let yourself be distracted from that goal. Demand accountability and results from your staff, your contractors, your team. You need to know the process as well as they do. You’ll never be short on promises, and unsolicited advice (like this). You’ll get fluffy strategies, and promises of silver bullets. Measure everything. Know your numbers. Demand a proper return.

You have a multitude of ways to get to 16,901 points. Your path to victory will be different than someone like Maxime Bernier, Jason Kenney, or Kellie Leitch. This is a data driven enterprise. For all Trump bloviates about being a self funded renegade, he has made smart hires, and build an enviable ground game. The modern campaign is a data driven exercise. You’ll lose if you run a 2006 campaign.

Know your product

You are your product. You are selling yourself, your ideas, and your vision for the country. You need to know what you want to accomplish, and how you plan on doing it. Your campaign is built off your credibility. You’ve no doubt seen candidates and campaigns built off policy, and those built off charisma. Aim for the former.

The actual “sale” in this race will be much different than others. You need to understand each type. For the interested non-member, you need to convince them to pay $25 to buy a Conservative Party membership. A big price to pay for many, especially given the economy. You need to convince the existing members that you are the guy for the job. This is usually easier, as they’ve paid their fees. All they need to do is mark a box. You need to sell yourself to the party activists. They are the ones that do the dirty work of licking envelopes, and making phone calls. Never a fun task. They need to know you are worth it.

The product isn’t actually sold until they submit their ballot with you as the top choice. A membership your team sells may vote for another candidate. You are up against a gifted team of salesmen and women. Don’t assume you have anything in the bag until the ballot is in the box.

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